1499-46-3

Usage

Uses

Used in Food Industry:
Methyl L-histidinate is used as a flavoring agent to enhance the umami taste in various food products, improving their flavor and taste profile.
Used in Pharmaceutical Industry:
Methyl L-histidinate is used as a dietary supplement due to its potential health benefits, such as antioxidant and anti-inflammatory properties, contributing to overall well-being and supporting the body's natural defenses.

InChI:InChI=1/C7H11N3O2/c1-12-7(11)6(8)2-5-3-9-4-10-5/h3-4,6H,2,8H2,1H3,(H,9,10)

Upstream product

• 77714-39-7 3-(1H-Imidazol-4-yl)-2-((E)-2-methyl-3-oxo-propenylamino)-propionic acid methyl ester 
• 67-56-1 methanol 
• 71-00-1 L-histidine 
• 69614-04-6 S-(+)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on 
• 71-00-1 L-histidine 
• 351-50-8 D-histidin 
• 6341-24-8 D-histidine monohydrochloride 
• 1604-44-0 N-α-trifluoroacetyl-L-histidine methyl ester 
• 17791-52-5 N-(tert-butoxycarbonyl)-L-histidine 
• 4467-54-3 l-histidine methyl ester dihydrochloride 
• 4467-54-3 histidine methyl ester hydrochloride 
• 645-35-2 L-histidine monohydrochloride 
• 4098-71-9 isophorone diisocyanate 
• 5619-10-3 L-histidine methyl ester dihydrochloride 

Downstream Products

• 6298-09-5 2,4,5-tris-benzoylamino-pent-4-enoic acid methyl ester 
• 1596-64-1 (+/-)-2-amino-3-(1⁽³⁾H-imidazol-4-yl)-propan-1-ol; dihydrochloride 
• 111562-61-9 N^α-(2-carboxy-benzoyl)-L-histidine-methyl ester 
• 65092-36-6 N^α,N^α-phthaloyl-L-histidine-methyl ester 
• 38972-84-8 N^α-(N-benzyloxycarbonyl-glycyl)-histidine 
• 16876-04-3 Benzyloxycarbonyl-Val-His-OMe 
• 110157-28-3 Z-L-Ser-L-His-OMe 
• 2489-13-6 GH 
• 17682-11-0 N^α-(N-benzyloxycarbonyl-glycyl)-histidine hydrazide 
• 37399-50-1 Z-Ile-His-OMe 
• 20223-80-7 Asp(His) 
• 74853-62-6 N^α,N^im-ditritylhistidine 
• 69323-20-2 Z-His-His-OMe 
• 137816-74-1 N^α-N^ω-Dibenzoyl Asparagine Methyl Ester 

Relevant academic research and scientific papers

Design, synthesis and evaluation of XZH-5 analogues as STAT3 inhibitors

Inhibition of the signaling pathways of signal transducer and activator of transcription 3 (STAT 3) has shown to be a promising strategy to combat cancer. In this paper we report the design, synthesis and evaluation of a novel class of small molecule inhibitors, that is, XZH-5 and its analogues, as promising leads for further development of STAT3 inhibitors. Preliminary SARs was established for XZH-5 and its derivatives; and the binding modes were predicted by molecular docking. Lead compounds with IC50 as low as 6.5 μM in breast cancer cell lines and 7.6 μM in pancreatic cancer cell lines were identified.

Novel metal chelating molecules with anticancer activity. Striking effect of the imidazole substitution of the histidine-pyridine-histidine system

Previously we have reported a metal chelating histidine-pyridine-histidine system possessing a trityl group on the histidine imidazole, namely HPH-2Trt, which induces apoptosis in human pancreatic adenocarcinoma AsPC-1 cells. Herein the influence of the imidazole substitution of HPH-2Trt was examined. Five related compounds, HPH-1Trt, HPH-2Bzl, HPH-1Bzl, HPH-2Me, and HPH-1Me were newly synthesized and screened for their activity against AsPC-1 and brain tumor cells U87 and U251. HPH-1Trt and HPH-2Trt were highly active among the tested HPH compounds. In vitro DNA cleavage assay showed both HPH-1Trt and HPH-2Trt completely disintegrate pUC19 DNA. The introduction of trityl group decisively potentiated the activity.

NITROGEN-CONTAINING COMPOUND, METHOD FOR MANUFACTURING THE SAME, AND OPTICAL FUNCTIONAL MATERIAL INCLUDING THE SAME

PROBLEM TO BE SOLVED: To provide a novel nitrogen-containing compound having luminescence property. SOLUTION: A nitrogen-containing compound represented by the following formula (I) in which RA, RB, R1, R2, R3, R4, and X are either one of the following (1) and (2). SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

NOVEL PYRROLO-LACTONE AND PYRROLE COMPOUNDS INDUCING CELLULAR GLUTATHIONE RECOVERY EFFECT AGAINST REACTIVE OXYGEN SPECIES, AND METHOD FOR PREPARING THE SAME

The present invention provides: a novel pyrrolo-lactone compound, which can be used as an improved pain therapeutic agent containing various substituents by using glucose and ribose as reducing sugars and conducting a reaction with various kinds of natural and unnatural amino acids; and novel pyrrolo compounds produced during a process of manufacturing the same. The novel pyrrolo-lactone and pyrrole compounds are substances which can be used as improved pain therapeutic agent by having increased restoration ability of glutathione in living cells against reactive oxygen species.COPYRIGHT KIPO 2019

Histidine–dialkoxyanthracene dyad for selective and sensitive detection of mercury ions

Histidine-dialkoxyanthracene (HDA) was synthesised as a turn off type fluorescent sensor for fast and sensitive detection of mercury ions (Hg2+) in aqueous media. The two histidine moieties act as ‘claws’ to selectively complex Hg2+. The binding ratio of HDA to Hg2+ was 1:1 (metal-to-ligand ratio). The association constant for Hg2+ towards the receptor HDA obtained from Benesi–Hildebrand plot was found to be 3.22?×?104?M?1 with detection limit as low as 4.7?nM (0.94?μg/L).

Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host?Guest Complexes with a Bis(zinc porphyrin) Tweezer

A stiff-stilbene-linked bisporphyrin tweezer with inherent helicity was used for exciton-coupled circular dichroism (ECCD) characterization of a series of monotopically binding amine guest molecules. CD signals were observed for a variety of monoamines at relatively low tweezer/amine (host/guest) ratios between 1 : 10 to 1 : 70. For the amines producing the most intense CD signals, a binding stoichiometry of 1 : 2 was found. A likely explanation is the presence of guest-guest interactions in the complexes. This is supported by the correlation observed between CD signal intensity and magnitude of possible noncovalent binding between the guests, which can be divided into three groups showing no, moderate and strong response, respectively. Further support for this rationalization comes from molecular modelling.

Discovery of a Membrane-Active, Ring-Modified Histidine Containing Ultrashort Amphiphilic Peptide That Exhibits Potent Inhibition of Cryptococcus neoformans

The new structural classes of ultrashort peptides that exhibit potent microbicidal action have potential as future drugs. Herein, we report that C-2 arylated histidines containing tripeptides His(2-Ar)-Trp-His(2-Ar) exhibit potent antifungal activity against Cryptococcus neoformans with high selectivity. The most potent peptide 12f [His(2-biphenyl)-Trp-His(2-biphenyl)] displayed high in vitro activity against C. neoformans (IC50 = 0.35 μg/mL, MIC = MFC = 0.63 μg/mL) with a selectivity index of >28 and 2 times higher potency compared to amphotericin B. Peptide 12f exhibited proteolytic stability, with no apparent hemolytic activity. The mechanism of action study of 12f by confocal laser scanning microscopy and electron microscopy indicates nuclear fragmentation and membrane disruption of C. neoformans cells. Combinations of 12f with fluconazole and amphotericin B at subinhibitory concentration were synergistic against C. neoformans. This study suggests that 12f is a new structural class of amphiphilic peptide with rapid fungicidal activity caused by C. neoformans.

Unveiling and tackling guanidinium peptide coupling reagent side reactions towards the development of peptide-drug conjugates

Peptide coupling reagents and especially uronium/guanidinium salts have been extensively utilized in solid-phase peptide synthesis. However, the impact of these reagents in solution phase synthesis, normally used in the formation of peptide-drug conjugates (PDCs), has not been fully explored. Herein, we identified that when guanidinium salts are used in classical peptide coupling conditions, besides leading to the formation of amide bonds, a uronium derivative can also be installed on specific amino acid scaffolds. The formation of this side product depends on the reaction conditions, as also on the nucleophilicity of the susceptible groups. Conditions to avoid this side product formation and a putative reaction mechanism describing its formation are reported.

Rational design of a highly selective fluorescent sensor for l-histidine detection in aqueous solution

Computational studies in combination with experimental research were used to design a new rapid, selective and sensitive "turn-on" fluorescent sensor (H3) for l-histidine, which can be first quenched by Ni2+ and then recovered upon addition of His.

SILOXANE POLYMERS WITH A CENTRAL POLYSILOXANE POLYMER BLOCK WITH TERMINAL ORGANOFUNCTIONAL RADICALS COMPRISING UREA AND/OR CARBAMATE GROUPS AND AMINO ACID RADICALS

The invention relates to siloxane polymer comprising a central polysiloxane polymer block B with organofunctional radicals, which are terminal or bonded laterally on the polymer block, comprising IPDI and amino acid derivatives which are covalently bonded via a hydrophobic or hydrophilic linker group Q1′, Q2′, and to compositions comprising these siloxanes. Furthermore, processes for their preparation and their use are disclosed.